Changes in Water Content during Metamorphosis of the Housefly,Musca domestica |
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| Authors: | Takuji Tsukamoto Ken Kihata Takashi Inaba Masaru Funatsu |
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| Affiliation: | 1. Department of Agricultural Chemistry, Saga University, 1-Honjo, Saga 840, Japan;2. Department of Applied Microbial Technology, The Kumamoto Institute of Technology, 4–22–1 Ikeda, Kumamoto 860, Japan |
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| Abstract: | The synthesis of ( – )-cis-neocnidilide (1), a stereoisomer of neocnidilide (2) having inhibiting activity against mycotoxin-producing fungi, is described. ( ±)-(E)-1,3-Nonadien-5-ol was kinetically resolved to give (S)-13, which was converted to (S)-triene ester 8. The intramolecular Diels-Alder reaction of 8 afforded a mixture of 12 and 10. The dihydro derivative 14, obtained by catalytic hydrogenation of 12, was transformed via trimethylsilylketene acetal into α-bromolactone 19, which upon treatment with DBU in toluene, gave rise to ( – )-cis-neocnidilide (1). |
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